{{short description|Chemical compound}} {{Drugbox | Verifiedfields = | Watchedfields = | verifiedrevid = | IUPAC_name = (8''R'',9''S'',10''R'',13''S'',14''S'',17''S'')-17-hydroxy-10,13-dimethyl-17-propyl-2,6,7,8,9,11,12,14,15,16-decahydro-1''H''-cyclopenta[''a'']phenanthren-3-one | image = Topterone.svg | image_class = skin-invert-image | width = 250px
<!--Clinical data--> | tradename = | pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> | pregnancy_US = <!-- A / B / C / D / X --> | pregnancy_category = | legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 --> | legal_CA = | legal_UK = | legal_US = | legal_status = | routes_of_administration = Topical
<!--Pharmacokinetic data--> | bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion =
<!--Identifiers--> | CAS_number_Ref = | CAS_number = 60607-35-4 | CAS_supplemental = | ATC_prefix = | ATC_suffix = | PubChem = 9797605 | DrugBank_Ref = | DrugBank = | ChemSpiderID_Ref = | ChemSpiderID = 39526 | UNII = 77WPB17ZK1 | synonyms = WIN-17665; Propyltestosterone; 17α-Propyltestosterone; 17α-Propylandrost-4-en-17β-ol-3-one
<!--Chemical data--> | C=22 | H=34 | O=2 | SMILES = CCCC1(CCC2C1(CCC3C2CCC4=CC(=O)CCC34C)C)O | StdInChI_Ref = | StdInChI = 1S/C22H34O2/c1-4-10-22(24)13-9-19-17-6-5-15-14-16(23)7-11-20(15,2)18(17)8-12-21(19,22)3/h14,17-19,24H,4-13H2,1-3H3/t17-,18+,19+,20+,21+,22+/m1/s1 | StdInChIKey_Ref = | StdInChIKey = LZSOOHLAZHOTHJ-GUCLMQHLSA-N }}
'''Topterone''' ({{abbrlink|INN|International Nonproprietary Name}}, {{abbrlink|USAN|United States Adopted Name}}) (developmental code name '''WIN-17665'''), also known as '''17α-propyltestosterone''' (or simply '''propyltestosterone''') or as '''17α-propylandrost-4-en-17β-ol-3-one''', is a steroidal antiandrogen that was first reported in 1978 and was developed for topical administration but, due to poor effectiveness, was never marketed.<ref name="Elks2014">{{cite book| vauthors = Elks J |title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=RA1-PA294|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=1–}}</ref><ref name="FerrariChakrabarty1978">{{cite journal | vauthors = Ferrari RA, Chakrabarty K, Beyler AL, Wiland J | title = Suppression of sebaceous gland development in laboratory animals by 17alpha-propyltestosterone | journal = The Journal of Investigative Dermatology | volume = 71 | issue = 5 | pages = 320–323 | date = November 1978 | pmid = 712108 | doi = 10.1111/1523-1747.ep12529809 | doi-access = free }}</ref><ref>{{cite book | vauthors = Rasmusson GH | chapter =Chapter 18. Chemical Control of Androgen Action | title = Annual Reports in Medicinal Chemistry |date=1986 |volume=21 |pages=179–188 (183) |doi=10.1016/S0065-7743(08)61128-8 | chapter-url=https://books.google.com/books?id=qsFCGskRHZQC&pg=PA183 |publisher=Academic Press|isbn=978-0-08-058365-5}}</ref><ref name="pmid7339330">{{cite journal | vauthors = Ferrari RA, Chakrabarty K, Creange JE, Beyler AL, Potts OG, Schane HP | title = Endocrine profile of topterone, a topical antiandrogen, in three species of laboratory animals | journal = Methods and Findings in Experimental and Clinical Pharmacology | volume = 2 | issue = 2 | pages = 65–69 | date = April 1980 | pmid = 7339330 }}</ref><ref name="ChakrabartyFerrari1980">{{cite journal | vauthors = Chakrabarty K, Ferrari RA, Dessingue OC, Beyler AL, Schane HP | title = Mechanism of action of 17 alpha-propyltestosterone in inhibiting hamster flank organ development | journal = The Journal of Investigative Dermatology | volume = 74 | issue = 1 | pages = 5–8 | date = January 1980 | pmid = 7351494 | doi = 10.1111/1523-1747.ep12514560 | doi-access = free }}</ref><ref>{{cite book | vauthors = Marsden JR, Shuster S | chapter = The Treatment of Acne |title=Pharmacology of the Skin II: Methods, Absorption, Metabolism and Toxicity, Drugs and Diseases| chapter-url= https://books.google.com/books?id=GvDxCAAAQBAJ&pg=PA490|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-3-642-74054-1|pages=490–}}</ref>
== See also == * Steroidal antiandrogen * List of steroidal antiandrogens
== References == {{Reflist|2}}
{{Androgen receptor modulators}}
Category:Abandoned drugs Category:Androstanes Category:Anti-acne preparations Category:Steroidal antiandrogens
{{Steroid-stub}} {{Dermatologic-drug-stub}}